Weekend in Essex: Connecticut’s cutest town

Essex, Connecticut is often named one of the best small towns in America. A dozen years ago, my parents went to the annual boat show in this charming little enclave on the shores of the Connecticut River and fell so deeply in love that they thought about relocating from Cape Cod. They didn’t make the move, but every time I visit Essex, I wonder what it would have been like to have a home away from home in Connecticut’s cutest town.

Renee Adams is someone who took that leap. She and her family had been living in Brooklyn, but when the pandemic hit they started dreaming about an easier way of life. So they bought a 200-year-old farmhouse in Essex and never looked back. “I love the proximity to the water, and there’s so much to do: shopping, restaurants, state parks, hiking,” she says. “​​And the town has a parade on Main Street for just about everything.” Soon after moving here, Renee discovered an old barn for sale—and a business was born. She transformed it into a highly Instagrammable rental called the River Barn which quickly attracted a following of urbanites in search of weekend escapes.

But before we go deeper, let’s talk details. The town of Essex is actually made up of three small villages—Essex, Centerbrook, and Ivoryton—and each of these hamlets has its own downtown. This area has a deep history: Essex used to be a thriving center for building wooden sailing ships, and George Washington vacationed here back in the day.

Now, an influx of visionaries like Renee are helping put a modern spin on this historic town. Jennifer and Steven Lieberman are two other pandemic-era newcomers. The couple, who also have a craft brewery in Santa Monica, California, decided to expand to the East Coast. Their new Surfridge Brewing Company is located in a refurbished factory called Witch Hazel Works, where they are combining a West Coast surf vibe with craft brews and a locavore gastropub. What appealed to them: “It’s great to be part of a growing community that has so much history—houses that were built in the 1700s, one of the last working steam trains in the country, and a hotel where George Washington used to stay,” says Steven.

That famous presidential vacation spot is The Griswold Inn, which opened in 1776 and is one of the oldest continuously operated hotels in America. Co-owner Joan Paul—who grew up in Essex—and her family are fiercely protective of this landmark space that they are helping preserve for generations to come. "We don't feel like we truly own this inn. We are just stewards of this property and this wonderful piece of history,” says Joan.

So let’s head to Essex for a weekend of historic charms, new finds, and an IPA or two.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

While there aren’t many places to stay in Essex, the quality of the accommodations is top-notch.

“The Gris” (as everyone calls it) started welcoming shipbuilders and sailors back in 1776. Spread out over several historic buildings, the landmark property is a piece of living history with one of the largest collections of maritime artwork in the country and rare artifacts that help tell the story of this country's founding. Every antique-decorated room is different; some have fireplaces.

With its chic interiors and thoughtful amenities—a collection of vinyl records, an acoustic guitar—it’s no wonder Condé Nast Traveler named this converted barn the coolest Airbnb in Connecticut.

At this 22-room country inn built in 1889, you can book a couples massage, have a romantic dinner at the restaurant set to live acoustic music, or just enjoy the peaceful setting.

This spacious three-bedroom farmhouse is a quiet sanctuary conveniently located right near the Surfridge Brewery and the Essex Steam Train.

From elevated coffee shops to farm-to-table restaurants, Essex has some delicious food options. Here’s our highly curated hit list.

Essex Coffee & Tea Co in Essex - A gathering spot for its fresh-brewed coffee, homemade pastries, and park-like setting in the center of Essex.

Savour Cafe and Bakery in Centerbrook - “This bakery is New York-worthy,” says Renee Adams. Check out the daily specials like a croissant with ham, brie, and apricot mustard.

Deep River Roasters in Centerbrook - Located in the up-and-coming Witch Hazel Works factory, this micro-roastery is making a name for itself with its artisanal blends and treats like maple bacon chocolate chip cookies.

Surfridge Brewing Company in Centerbrook - This new West Coast-style brewery serves inventive brews like a Belgian ale aged in pinot noir barrels and a Belgian white ale with pink peppercorn and pink grapefruit. Plus, you’ll find live music and delicious bites, like cheese boards from a local purveyor and oysters that were just pulled from the water that morning.

Olive Oyl’s in Essex - “A really unique space in an old gas station on Main Street that I frequent all the time,” says Renee.

Bun on the Run in Centerbrook - Steven Lieberman is a fan of this casual sandwich joint. “Don’t miss the bacon, egg, and cheese and the avocado toast,” he says.

Black Seal Seafood Grille in Essex - A nautically themed pub with sophisticated dishes like a grilled blackened swordfish with pineapple, cherry tomato, and cucumber lime salsa.

Scotch Plains Tavern in Essex - An upscale sports bar with live music and a menu of creative bites like a grilled peach salad and parmesan-crusted panko chicken.

The Griswold Inn in Essex - Wherever you choose to eat at the Gris, it’s always a special experience—from the four historic dining rooms to the Wine Bar to the Tap Room, which was built in 1735 as a schoolhouse. According to co-owner Joan Paul, fan favorite dishes include the prime rib and the fish and chips.

Carlson’s Landing in Essex - Set in the historic Essex Boat Works, this elegant restaurant is the place for fresh-caught seafood and craft cocktails. “A great place right on the water,” says Renee.

Essex Clipper Dinner Train in Essex - All aboard a beautifully restored 1920’s Pullman car that glides along the banks of the Connecticut River as you dine on a lavish four-course meal.

Chocolate Geeks in Essex - This mother-daughter chocolate shop developed a following for its truffle shots, but has now expanded to serve other delicious treats like bean-to-bar cookies.

Sweet P’s in Essex - “A great ice cream shop in downtown Essex,” says Steven.

From history to the arts, here are a few ways to get a culture fix.

Connecticut River Museum in Essex - Set on an old steamboat dock, this museum reveals the rich history of the river and the area's shipbuilding industry via permanent and rotating exhibits.

Ivoryton Playhouse in Ivoryton - This isn’t your average theater: Acting legends like Katherine Hepburn and Eva Gabor have appeared on its stage over the years.

Cooper & Smith Gallery in Essex - This is a serious gallery with more than 5,000 square feet of exhibition space showcasing contemporary artists.

Here’s where the locals go when they want to get a breath of fresh air in and around Essex.

Essex Steam Train & Riverboat Cruises in Essex - Take in the beauty of the Connecticut River Valley on a ride aboard the Essex Steam Train, with restored railroad cars pulled by a coal-fired locomotive. Or enjoy a cruise along the river on a vintage riverboat.

RiverQuest in Essex - This boat owned by the Connecticut River Museum runs wildlife-spotting cruises to spy on eagles and more.

Essex Land Trust in Essex - This land trust—a great resource for outdoor lovers—is committed to protecting natural spaces. "The Essex Land Trust has a myriad of trails throughout our three villages," says Joan Paul.

Essex Town Park in Essex - "A small but beautiful green space that looks out over Middle Cove," says Joan.

Essex is the place for independently owned boutiques with tons of personality.

The RiverLane in Essex - A former finance exec opened this chic new clothing boutique that would be equally at home in New York City.

Goods & Curiosities in Essex - The Griswold Inn’s shop sells reproductions from the hotel’s art collection, housewares, books, and one-of-a-kind products made by Connecticut artisans.

Toys Ahoy in Essex - Kids (and kids at heart) can’t get enough of this well-curated store with toys, games, books, and more.

Weekend Kitchen in Essex - Whether you love to cook or are just looking for a handy new tool, this kitchen store is culinary nirvana.